Lubricating composition



Reiscued Sept. 29;1942 it R 22,189

um-rs, stares A) Carl F. Prutton, Cleveland, and Albert K; Smith,

Shaker Heights, Ohio, assignors to The Lubri- Zol Development Corporation, Cleveland, Ohio,

. a corporation of Delaware No Drawing. ()riginai No. 2,255,085, dated September 9, 1941, Serial No. 241,606, November 21, 1938. Application for reissue July 23, 1942, Serial 'No. 52,116

13 Claims. (Ci. 252-=-'-5) In U. S. Patents Nos. 1,986,645 and- 1,986,651 it (Nata-The hydrogen'evolved by (2) probably is taught that the lubricating properties of a would act to reduce one or more of the organic lubricating composition may be materially imcompounds rather than to appear as free byproved and extreme. pressure characteristics imdrogen.)

parted to lubricants such as mineral lubricating 5 The correctness of the foregoing theory is suboil, by the addition thereto of minor amounts of stantiated by the fact that when a chlorinated halogenated carbon ring compounds. hydrocarbon is added to a hydrocarbon mineral This application is a continuation in part of oil and the mixture thoroughly'freed from moisco-pending applications Serial No. 31,720, now ture bythe action of -dehydrating agents, the film Patent No. 2,137,782, and Serial No. 170,500 filed strength is no more than that of the oil alone.

October 22, 1937, now Patent No. 2,204,620. 1 Exposure of the mixture to the atmosphere so It, has been explained thatthe reason why that it may absorb a slight amount of moisture such compounds thus improve the extreme preswill then cause an increase in the film strength. sure characteristics of the lubricant probably is Since the presence of a large amount of moisdue to the fact that such addition agents chemiture and especially-or free water is objectionable cally react with the bearing surfaces under the in a lubricant besides being a highly variable conditions imposed by relative movement and exfactor in normal service, it is advisable to supply treme pressure between the bearing surfaces to an oil soluble substitute for the same.

form a microscopic film of a metallic halide It is the principal object of this invention,

which prevents seizing between the bearing surtherefore, to provide a lubricating composition faces by acting as an anti-fluxing agent. as the type utilizing halogenated organic com- The halogenated carbon ring compounds were pounds as the extreme pressure addition agent indicated as preferable in said patents due to the but so modified as to be effective in the manner fact that such compounds are relatively stable, defined without being dependent upon the l. e., they donot readily hydrolyze in/the presence presence in the lubricating composition of some of moisture which usually occurs in varying addition-material such as water.

quantities in mineral oils. In other words, the Other objects of our invention will appear as halogenated carbon ring compounds are sufiithe descri ti n proceeds, ciently stable so that decompositlon-andattach T th accomplishment of the foregoing and thereof p the metallic Surfaces Occurs y related ends, said invention,then consists of the v in the areas where extreme press encolmmeans hereinafter fully described and particutered,i. e., on the bearing surfaces. larly pointed out in the claims.

One theory of the action of halogen com- The following description sets forth in detail P Specifically Chlorine C p in one approved combination of ingredients emcrea ine fi m Strength, assumes that, as above bodying our invention, such disclosed means indicated, under the stress of the rubbing action constituting however, t one of various forms of bearing surfaces in motion under load, chloin which t principle of t i ti may b rides of the bearing metals are formed on their used surfaces and exert an anti-fluxing effect in pre- Broadly Stated, this invention comprises t venting subsequent fusing of the two surfaces. 40 use as a'lubricant f oxygen and hamgenbearmg This surface reaction, however, to take place organic compounds and more pe ifi ally oxygen with sufficient effectiveness depends upon the and m- -m ganja ing cgmpounds y o y 0f the Chlorine compound as a Simuleither used alone or incorporated with any suittaneous intermediate reaction. These reactions ab1e n base, i may be expressed as follows The oxygen which is included in the molecule (L) RCI+'HZO HC1+ROH g of the addition agent acts to increase the effectiveness of the latter in raising the film (2) M+HC1%MC1+H strength of a mineral oil to which the addition where R is an organic radicle and M isone of agent is added or to improve the lubricating the metals of the bearing surfaces. 5 properties of the halogenated compound when cant.

' of improving the species and particularly 2 used without the addition of some other lubri- The oxygen probably acts in the same way as water in making possible the formation of hydrochloric acid as an intermediate step in the surface reaction above explained- By combining in a' single molecule the halogen and the oxygen atoms. a lubricant is affected in two ways:

First-The oxygen is always available at the exact point where required; and

second-The molecule is more strongly absorbed by metal surfaces than similar halogen compound which do not contain oxygen.

' The latter circumstance equivalent to an increase in compound at the bearing surfaces.

We have found that certainoxygen-containing organic ring compounds which have been chlorinated and added to a lubricating oil are capable properties of such oil, particuiarlyv when employed for thin-film" purposes. The addition of these certain oxygen containing organic ring compounds which have been chlorinated and added tothe lubricating oil have been found to improve the properties there- I I of to an even greater extent than certain similar chlorinated hydrocarbons, notably when added in very small amounts.

The halogen and oxygen-containing organic ring compounds added to a suitable 011 bas are, as above indicated, preferably of the chlorinated :the compounds which have been found to produce very satisfactory results; may be classified as follows, viz:

I. "Carbon ring type'compounds:

enhances the effect of small amounts of such compounds "because it is concentration of the ,ss,'1e'e ring structmes are of the heterogeneoustype and of the oxygen to the compound,

lubricating (a) 0f the aromatic, or allied type, includ- ,e f (3) Naphthenes, naphthenic acid, etc. Of mixed type such as oxygen and halogen-bearing derivatives of indene, hydrindene, hydranthracene,

e 1 II. "Heterogeneous ring" type compounds:

(a) of the aromatic or allied type including oxygen and halogen-bearing derivatives of pyridine, quinoline, etc.

(b) Other types such as oxygen and halogen-bearing derivatives of furan and its" derivatives pyrrole, etc.

Includedin Class 11 are two principal types of compounds, viz: Compounds in which .all of the and oi" thiophene,

) Hydrogenation products of benboth heterogeneous ring structures and carbon ring structures.

The foregoing 'compounds may also be classiiled ccording to the nature of the attachment viz:

I'tDirectly' attached to one or more carbon atoms, asin the cas of:

(1') Ether-sand analogus compounds.

(2') Compounds containing the 50-01! radicle, such as alcohols and other derivatives of carbinol (in cludlng phenols, cresols, naphthols etc).

(3') Compounds containing the carbonyl (=(b0) radicle, such as aldehydes, ketones, organic acids, esters and salts of organic acids, thio-acids and esters of thicac ds. (4') Compounds in which oxygen forms a part-of the ring structure, e. g.

furan and its derivatives; anthraquinone, etc.

l1. Indirectly attached through the means of some other atom, i. e..in[ the form of an inorganic radicle,-e. g.:

Amide Phosphate Arsenate Phosphite Arsenite Sulphate Chlorate Bulphite Chlorite Sulphinic acid Cyanate Sulphone Hydroxylamine Sulphonic acid Hypochiorite Bulphoxide Nitrate Thi cyanate Nitrite Isothiocyanate Nitro Thio-sulphate Nitroso Thio-phosphate Perchlorate hate The halogen and oxygen-bearing organic ring compounds of theester and salt type include compounds of the aromatic type which may be classified as follows: J 1. Esters and salts of an aromatic acid; 2. Esters formed by the combination of a phenol,

cresol. naphthol, etc. with an organic acid of either the fatty or aromatic type:

In addition to the gen, other substitu such as other aryl grou alkylgroups. and amino and substituted amino groups, imino, azo, hydrazo, hydrazine, nitrile, mercapto, sulphide, polysulphide.

Specific examples of may be substitution products, addition products, I formed by halogenation of the compound listed, or of intermediate compounds or by some other method.

Class ,I(a)-I(3) run-mac Acetanilide Acetophenone Aluminum phen'yl mer-' capto stearate Aluminum phenyl'stearate Amyl salicylate Amino phenol Anethole Aniline oleate Aniline stearate Anthraquinone Anthranol Azobenzoic acid Azophenol Benzaldehyde A Benzaldoxime Benzamide Benzyl sulphite Benzyl sulphone Benzyl thio-sulphate Borneo] Bornyl acetate Butyl azohenzoate Butyl esters of:

Pyrrole carboxyllc acid Thiophene carboxylic acid Butyl benzoate Butyl thio-benzoate Butyl ester of mercapto resolic acid Butyl ester .01 phenyl acetic acid Butyl ester of phenyl 1(a) --II' nan-Maw stearic acid 1(a) -I' (3) Butyl furoate II(b)'--I' (3) and (4') Butyl mercapto benzoate a 1(a) -I' (3') Butyl naphthenate 1(a) --I'-(3') Butyl phenyl ketone 1(a) --I' (3') Butyl toluate I I(a)-I'(3') Calcium naphthenate 1(a) -I' (3') Calcium phenyl mercapto stearate I(a)--I'(3') Calcium phenyl stearate Ha) --I' (3') Camphor 1(a) --I (2') Cinnamic acid and esters 1(a) -I' (3') Cresyl acetate 1(a) --I' (3') Cresyl naphthenate I) (3) --I' (3') Cresyl stearate Ha) -I' (3') Cyclohexanol 1(1)) (1) -I (2') Cyclohexanon I (b) 1) -I' (3) Decahydronaphthol 1%) (2) --I' (2') Dibenzoyldimethyl disulphide Dibenzoyldimethyl sulphide Dibenzoyl disulphide Dibenzoyl sulphide Dibenzyldisulphide Dibenzyl ether 'Dibutyl phthalate abuse Dihydroxy diphenyl sulphide Dinaphthyl ether and (3') i Dinaphthyl ketone Diphenyl "acetic acid and esters Dlphenyl ether Dixenyl ether Ethyl ester of phenyl acetic acid Ethyl naphthyl ether Ethyl salicyclic acid and esters Ethyl toluate Furan Furtural Furll Furoin Hexahydrophenyl acetate Hexahydrophenyl mercaptc stearate Hexahydrophenyl stearate Hydroxyazcbenzene Hydroxy-benzyl mercaptan Hydroxyd i p h e n yl amine Hydroxy-indene Hydroxy methyl aniline v Hydroxy phenyl lay drazine Hydroxyphenyl m e r captan Hydroxy-quinoline Hydroxythiophene lminophenol' Indoxyl i Ketopentamethylene Mercapto benzoic acid Mercapto rcsolic acid Methyl salicylate Methyl toluate Naphthol Naphthol ethyl ether Nitrodiphenyl Nitrosobenzene Nitrosophenol Nitrotoluene Phenol Plienyl acetate Phenyl acetic acid Phenyl amyl nitrate Phenyl amyl nitrite Phenyl amyl ether Phenyl benzoate .Phenyl ethyl alcohol and (3') run-1' (2') 1(a) I' (2) 1(0) -I' (2) run-41- rec-11' rec-11' A i I aaise Phenyl ethyl sulphone I(a)-II' Among the esters and salts, halogen deriva- Phenyl thyl thlosultives of which are likewise suitable for use as hate Hal-II addition agents, are the esters and salts which Phenyl hydroxylamine I(a)-1I' may be derived from the aromatic acids listed Phenyl mercapto stea-i 5 immediately above and mono and polyhydric alrate I(a)-I'(8') cohols, or other hydroxy compounds (including Phenyl mercapto stearic i phenols). Specific examples oi such alcohols and acid and esters 1(a) -I'(3') hydroxy compounds are those specincallyldenti- Phenyl naphthenate I b) (3)I'(3') fled under (6) on page 5.

Phenyl naphthyl ketone I (a)--I'(3') l0 Among the salts of aromatic acids, the halogen- Phenyl nitrite I(a)-II' bearing derivatives or which may also be em- ,Phenyl oleate I(a)-I'(3') ployed as addition agents, are the salts or the Phenyl oxydlsulphide [(a) I'(3') aromatic acids listed above, including the sodium. Phenyl phenol I(a)I'(2') calcium, aluminum, magnesium, zinc and lead P nyl phenyl-acetate I(a)I'(3') is salts, and salts derived from ammonia, substi- Phenyl phenyl-naphtuted ammonias, and other organic bases such as thenate --I(b) (3)I'(3') quinoline and pyridine. Ph ny p eny m e I B- I'( A very important group or esters, halogen- P en prupionic acid bearing derivatives oi which are particularly (i Ester! a suited for use as addition agents, especially in Phenyl propyl alcohol I(a)I'(2') certain types 01' lubricants, are the esters of al- Phenyl stearate I lie) -1'(3') 'cohols of the benzenoid type. Specific examples Phenyl stearic acid I(a)I'( ,3') or'such alcohols are the following: gyyfigine stearate v II(a)-I (3 Benzyl alcohol J 26 Phen leth lalcohol Sodium phenylmercapq i B y y tostearate run-rise enz-hydml I Tri phenyl carbinol Sodium phenylstearate I(a)I (3 h 1 Sodium thiobenzoate run-ms) Phenyl Stearanilid I(a)I'(-3') Phenyl Tertiary amyi phenol l'(a)-(I) (2) 8o 1 Fun-m] who! 'Ihiobenzoic acid I(a)l'(3') Naphtmbenzy Toluic acid l.'(a)-I'(3') Cmmmyl Tricresyl phosphate I(a)II' A This class of esters may be derived from alco- Triphenyl arsenate ITa)II' hols oi the benzenoid type, such as those listed Trlphenyl arsenite I(a)II' above and organic acids, ither aliphatic or aro- Triphenyl phosphate I (a)-II' matic or from such alcohols and inorganic acids. Triphenyl phosphite Ital-II Examples of such organic and inorganic acids Tri-tertiary amyl phenare those listed under (6) (b) on page 5.

yl -phosphate Hal-II 40 The class of unsaturated oxygen compounds is Zinc benzoate I(a)I(3') particularly suited, after haiogenation or halogen Zinc phenylstearate I(a)-I'(3') treatment, for use, as addition agents in accord- In the following table are given examples of ance with our invention Ihe following is aromatic acids, halogen-bearing derivatives of classification of these unsaturated oxygen which may be employed as addition agent. in pounds along with specific examples of the variaccordarice with our invention: groups within tmsjub'class:

Benzoic geld v (l) Unsaturated alcohols, e. g.-

Benzoic acid derivatives Vinyl ethyl alcohol Azobenzoic acid ll?! 81001101 Mercapto benzoic acid CIOWIIYI 81001101 Lauryl benzoic acid Oleyl alcohol Salicylic acid Propargyl alcohol Salicylic acid derivatives i Ethyl salicylic acid 5 (2) jfgjg fg Carboxylic acid icrotonaldehyde Carboxylic acid derivatives Hexadiemfl Pyrrole carboxylic acid octatri- I 'I'hiophene carboxylic acid Acetic acid i Acetic acid derivatives Pmpugync amehyde Phenyiacetic acid (3) Unsaturated ketones, e. g. Diphenyl acetic acid I Allyl acetone I Stearic acid I, 1 Di-allyl ketone Stearic acid derivatives o5 Mesityl oxide Phenyl stearic acid Phorone Phenyl mercapto stearic acid Vinyl lauryl ketone Xenyl stearic acid Acetylenic ketones (e. g.. Naphthyl stearic acid A R-CEC-CO-R') Tolyl stearic acid 7 such as:

Furoic acid Allylenemethyl ketone i Cinnamlc acid d V Allylene lauryl ketone Phthalic acid Ketenes Teluic acid \Ketene Mercapto rosolic acid d 7s Acetyl ketene v 22,189 (4) Unsaturated ethers, e. g.-- Aromatic acids, including: Di-vin'yl ether Benzoic acid Di-allyl ether Phthalic acids Allyl ethyl ether Salicylic acid Vinyl ethyl ether 5 Anthrenfllc acid Allyl iso-amyl ether cmamic id Any] lauryl ether cyclgi-alitpalatlis acids, including:

ap e ac s Bropargyl ethyl Hexahydrobenzoic acid Unsaturated acldsl0- Heterocyclic acids including:

1 7 Vinyl acetic acid mole acid .Vinyl acrylic acid Pyrrol carboxylic acids Vinyl glycolic acid Inorganic acids, including: Acrylic acid Hydro-halogen acids Crotonic acid 5 Oxy-halogen acids (ileic acid 1 Sulphurous acid Linoleic acid Sulphuric acid Maleic acid Thiosulphuric acid Fumaric acid Carbonic acid Linolenic acid o Thiocarbonic acids Elaeostearic acid Hydrogen sulph e Propiolic acid Phosphorous acid Stearolic acid' Thlophosphoric acids Phosphoric acid (6) Unsaturated esters, e. g. y Tmophosphoric acids (a) Esters ofwunsaturated acids (e; .g. those Cyanic acid listed under (5) above as well as un- Thiocyanic acid saturated aromatic acids such as cin- Hydm yanic acid namic and coumaric) with monoand Boric acid poly-hydric alcohols, onother hydroxy 3 (7) Salts of unsaturated acids, including thecompounds (including phenols). amples of such alcohols compounds are: Methyl alcohol Ethyl alcohol Propyl alcohols Butyl alcohols Amyl alcohols Lauryl alcohols Cetyl alcohols Benzyl alcohol Furiuryl alcohol Tetrahydrofurfuryl alcohol Ethylene glycol Propylene glycol Di-ethylene glycol Glycerol Erythritol L Phenol Polyhydroxy-benzenes Alkyiated phenols Naphthols and hydroxy Unsaturated alcohols (e. 3. those listed under (1) above) (11) Esters of unsaturated alcohols (e. g. those listed under (1) above) with organic acids, either aliphatic or aromatic, or with inorganic acids. .Examples of such acids are aliphatic acids, including- Saturated acids, such as:

Acetic acid Propionlc acids Butyric acids Laurie acids Palmitlc acid Stearic acid oxalic acid Citric acid Lactic acid Giycolic acid Malonic acid j Unsaturated acids, such as those listed under (5) above. 1 I

Ammonium and substituted ammonium Sodium Aluminum Calcium Magnesium Zinc Lead Salts of unsaturated acids generally, and more specifically of such acids as those listed under (5) above and of unsaturated aromatic acids.

In addition to the compounds listed above, commercial products comprising complex mixtures of unsaturated oxygen-bearing organic compounds may be used as the unsaturated" reactant. Examples of such materials are the fatty oils of unsaturated character, e. g.:

Castor oil China-wood oil Corn oil Cottonseed oil Croton oil Lard oil Y Linseed oil Menhaden fish oil Rape seed oil Soya bean oil Sperm oil Useful additional unsaturated oxygen compounds which may be derived from any or the above fatty oils are, e. g.-

(l) Acids, extractedfrorn the oils by direct bydrolysis, or by saponification and subsequent hydrolysis, or otherwise.

(2) Esters, produced by esterifying the acids of (l) e. g. to form esters analogous to any of those listed under ('6) inTable No. 2.

' (3) Soaps, produced by saponiiying the oils directly or by neutralizing the acids of (l) with alkalies, e. g. to form salts analogous to those listed under (7) in Table No. 2.

The unsaturated oxygen compounds are of particular importance and may,

therefore, be

. tuted benzenes where two or classified in further detail according to the nature of the attachment of the oxygen atom to the molecule, viz:

' Table No.11

such salts of both inorganic and orf ganic bases) and salts or (4') Compounds in part of the ring structure, e. g. tuna and its derivatives} etc.

(5') Compounds with where the oxygen-ls to a .carbon atom.

Arsenites Hypochlorites Phosphites. Thiophosphates Thiophosphites p-hydroxylamines Borates II. Indirectly attached through the means of some other atom, i.e., in the form of an inorganic radicle, e. g.-

Arsenate I Chlorate Chlorite Cyanate a-hydroxylamine Nitrate Nitrite Nitro Nitroso Oxlme Perchlorate Phosphate Sulphate 1 Bulphite t Sulphinic acid- Sulphone Sulphonic acid Sulphoxide Thiophosphate 'I'hlophosphite 'I'hio-sulphate (Note.This class includes salts bases with inorganic oxy-acids.)

In addition to the unsaturated 'compounds thio-acids and esters thio-acids directly attached e. K.

of organic above described, certain unsaturated cyclic compounds are also of use, such as the cyclo-oleflnes (c. g2 cyclo-hexen'e) and derivatives of them.

As 'a matter of convenience, the halogen and voxygen-containing substituted diphenyl's, as well as the halogen and oxygen-containing substiare directly linked, may be inclusively referred to as halogen and oxygencontaining substituted p l nh nyls. a

a This invention also contem'plates the use of acids"(such as those included among the unsaturated oxygen-bearing which O gen forms a an inorganic radicle I aromatic compound;

Examples of acids, esters and salts of addition agents may, for most uses, be added in l The optimum amount of the halogen comnd to be employed is usually dependent upon 1 various considerations such as its cost, the charcompounds referred to acter measure upon the above) with an aromatic'compound in the presfaces is reduced, especially the more viscous comwhere the particular require thick film lubrication, the

pounds. When, however, pounds are employed, or use does not so-called addition agents may, as previously indicated, be employed in their purestate.

, Experiments have shown that when compounds which readily hydrolize, such as chlorinated open chain compounds, .are added to the oily base, hydrolysis will take place to such an extent that the metal parts of any machine being lubricated will be seriously attacked and corroded by the acid generated. On the other hand, the addition of chlorinated organic ring compounds of the above enumerated class does not cause corrosion.

Certain of the halogen and oxygen-bearing open chainor aliphatic compounds, in their pure state, or when added to a suitable base do result, however, in a lubricant particularly, suitable for certain purposes. Examples of the foregoing are halogenated fatty oils such as chlorinated cottonseed oil and chlorinated 'cocoanut oil. As above indicated, such compounds readily hydrolize and while thus not preferred as a lubricant for use in the crank case of internal combustion engines, are nevertheless, admirably suited for use as lubricants in metal working such as drawing, extruding, rolling, etc., where the lubricant is in contact with the metallic surface for only relatively a short length of time and where the very slight amount of corrosion which may result is not particularly objectionable. Furthermore, such compounds are admirably suited for' use in lubricants in die drawing or similarly working certain corrosion resistance materials such as stainless steel and the like.

With regard to the stability of the organic ring compounds contemplated, the most resistant to hydrolysis of the halogen are those. in

, which the halogen is directly attached to an atom which is part of a benzenoid ring structure. Examples of such ring structures are aryl groups such as the phenyl and naphthyl groups. In any case, for most uses, it is preferred to have the halogen attached to an atom which ispart of an organic ring structureand'especially a sixmembered'organic ring structure. w

The compositions comprising our invention have certain advantages when used as a lubricant of which the following may FirstF-By the use of this composition, it ispossible to extend the pressure range between the bearing surfaces because of the reduced tendency for bearing surfaces so lubricated to become scored or to seize at higher pressures than are allowable with ordinary lubricants.

Second.-The friction between the bearing sursure range, below that obtained with ordinary lubricants. of our invention ber of classes and specific examples of addition agents, the haloderlvatives or whicnare contemplated for use as addition agents in the preparation of lubricating compositions in accordance with our invention. Many of these materials themselves, 1, 'e., the unhalogenated materials named, as well as the halogen-free analogs of the halogenated or halogen-bearing materials named, may be employed to advantage in lubricating compositions sincemany of such posses valuable properties as addition agents.

These unhalogenated materials may be used be mentioned:

in the higher pres-.

, combination,

" base and a I methylsallcylate.

as the sole addition agent to impart improved lubricating propertiesto a mineral oil (or other lubricating medium) or may advantageously be used in conjunction with other addition agents, such as organic halogen compounds, organic phosphorus compounds (e. g. esters of phosphoric and phosphorous acids), organic sulphur compounds, soaps, oiliness agents, oxidation inhibitors, viscosity index improvers, or such other addition agents as may or other purposes.

Other modes of applying the principle of our invention may be employed instead of the one explained, .change being made as regards the materials employed, provided the ingredients stated by any of the following claims or the equivalent of such statedingredients be employed.

We, therefore, particularly point outand distinctly claim as our invention: 1. A lubricating composition comprising a major proportion of mineral lubricating oil and a minor proportion of a halogen-bearing ester of an unsaturated alcohol and an aromatic acid.

2. A lubricating composition comprising in combination, a major proportion of a suitable oil base and a minor proportion of a halogenated ester of an aromatic acid.

3. A lubricating composition comprising in combination, a major proportion of a suitable oil base and a minor proportion of a halogenated alkyl ester of an aromatic acid.

4. A lubricating composition comprising in combination, a major proportion of a suitable oil base and a minor proportion of a halogenated ester of a hydroxy aromatic acid. 7

5. A lubricating composition comprising in base-and a minor prbportion of a ester of a hydroxy benzoicacid.

6. A lubricating composition comprising in combination, a major proportion of a suitable oil base and a minor proportion of a halogenated ester of a hydroxyl aryl carboxylic acid.

7. A lubricating composition comprising in proportion of a suitable oil base and a minor proportion of a halogenated alkyl ester of a hydroxy aryl carboxylic acid.

. 8. A lubricating composition comprising in a major proportion of a suitable oil 1 combination, base and a minor proportion of a halogenated alkyl ester of a hydroxy aromatic acid.

9. A lubricating composition comprising in combination, a major proportion of a suitable oil minor proportion of a halogenated .alkyl ester of a hydroxy benzoic acid.

10. A lubricating composition comprising in combination, a major proportion of a suitable oil base and a minor proportion of a halogenated ester of salicylic acid.

l1. Alubricating composition comprising in combination, a major proportion of a. suitable oil base and a-minor proportion of a halogenated alkyl ester of salicylic acid.

12. A lubricating composition comprising-in combination, a major proportion of a suitable oil base and a minor proportion of halogenated methyl salicylate.

13. A lubricating composition comprising in combination a major proportion of a suitable oil base and a minor proportion of chlorinated cam-r. rnu'rron. ALBERT K. sm'm.

be employed for the same' a major proportion of a suitable oil halogenated 

